Hydrochloric Acid → (6-Chloronaphthalen-2-yl)methanol

HRID 973295Notes

Reaction equation

HRID 973295 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](OC)=[O:13])[CH:6]=[CH:5]2.Cl.O>CCOCC.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][OH:13])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13384252Methyl 6-chloro-2-naphthoate

Product 1

HCID 13384253(6-Chloronaphthalen-2-yl)methanolYield 98%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A solution of the methyl 6-chloro-2-naphthoate (111 g.) in ether (2.5 l.) is added, dropwise below 25° C. under nitrogen, to a stirred mixture of ether (250 ml.) and a 70% solution (250 ml.) of sodium dihydro-bis-(2-methoxyethoxy)aluminate in benzene during 1 hour. The mixture is stirred for a further 30 minutes and 2N-hydrochloric acid (250 ml.) is added cautiously. The solution is decanted from undissolved solid, and concentrated hydrochloric acid is added to the solid until it dissolves. The two solutions thus obtained are combined, and ether (1 l.) and a mixture of ice and water (1 l.) are added. The ethereal layer is separated, and the aqueous phase extracted with ether. The ethereal solutions are combined, washed with water, dried and evaporated to give 6-chloro-2-hydroxymethylnaphthalene (95 g.) which may be further purified by crystallisation from toluene to give material of m.p. 134°-137° C.

Workup

  1. customThe solution is decanted from undissolved solid, and concentrated hydrochloric acid
  2. additionis added to the solid until it
  3. dissolutiondissolves
  4. customThe two solutions thus obtained
  5. additionare added
  6. customThe ethereal layer is separated
  7. extractionthe aqueous phase extracted with ether
  8. washwashed with water
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-d4e75198cc78479cbc01eedd77402b17
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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