HCID 13210860, compound → HCID 13210862, compound

HRID 1905976Notes

Reaction equation

HRID 1905976 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][C:10]=1[Cl:27])C1C=CC=CC=1>Br.C(O)(=O)C>[Cl:27][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 13210860HCID 13210860, compound

Product 1

HCID 13210862HCID 13210862, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

The 1-benzyloxy-2-chloro-4-(2-phenethyloxyethoxy)-benzene obtained according to the preceding paragraph was stirred in 20 ml of 48% hydrogen bromide in glacial acetic acid at 25° C. for 30 minutes. The solution was evaporated to dryness and the residue was partitioned between 2N aqueous sodium hydroxide and diethyl ether. The aqueous phase was acidified to pH 6 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, filtered and evaporated to give 2.06 g (76%) of 2-chloro-4-(2-phenethyloxyethoxy)phenol in the form of an oil which was homogeneous according to chromatography.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was partitioned between 2N aqueous sodium hydroxide and diethyl ether
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9c42c10bba0144f7ae878233e3deb12e
Source dataset
uspto-grants-1987_03
Patent number
US04649160

Reaction notes

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