Hydrochloric Acid → 1-Cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene

HRID 903150Notes

Reaction equation

HRID 903150 reaction equation
[C:1]([C:3]1([O:13][Si](C)(C)C)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2].Cl>C(O)C>[C:1]([C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117469071-Trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 157503811-Cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The silyl cyanohydrin of Example 3 (40.7 g, 165 mol) was dissolved in 300 ml ethanol and perfused at 0° C. with hydrogen chloride for 30 minutes. After an additional 16 hours at 0° C. the mixture was evaporated in vacuo to an oil. This was taken up in chloroform and washed with 2×100 ml sodium bicarbonate, 1×80 ml water, 1×80 ml brine, dried over magnesium sulfate, filtered, and evaporated in vacuo to a residue which partially crystallized. This solid was triturated with 10% ethereal hexane 17.6 g (62%) mp 55°-59° C. (69°-75° C. after recrystallization from ether/hexane).

Workup

  1. customAfter an additional 16 hours at 0° C. the mixture was evaporated in vacuo to an oil
  2. washwashed with 2×100 ml sodium bicarbonate, 1×80 ml water, 1×80 ml brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo to a residue which
  6. custompartially crystallized
  7. customThis solid was triturated with 10% ethereal hexane 17.6 g (62%) mp 55°-59° C. (69°-75° C. after recrystallization from ether/hexane)

Sources & evidence

ORD record
ord-f22c45690f494ba3b543d753329e2868
Source dataset
uspto-grants-1980_10
Patent number
US04226875

Reaction notes

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