Water → 2-benzoyloxymethylene-6-methoxy-1-Tetralone

HRID 487664Notes

Reaction equation

HRID 487664 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH:11]=[C:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[C:13]1=[O:24].O>N1C=CC=CC=1>[C:1]([O:10][CH:11]=[C:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[C:13]1=[O:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 2643163,4-Dihydro-2-(hydroxymethylene)-6-methoxy-1(2H)-naphthalenone

Product 1

HCID 538779652-benzoyloxymethylene-6-methoxy-1-TetraloneYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (11.4 ml, 0.1 mole) was added to a stirred solution of 2-hydroxymethylene-6-methoxy-1-tetralone 2 (10 g, 0.05 mole) in about 60 mL of pyridine at about 0°. After the addition was complete, the mixture was stirred at about 23° for about 2 hours then poured into water. The solid was filtered and washed with water. The pure product was obtained by recrystallization from methanol to yield 2-benzoyloxymethylene-6-methoxy-1-Tetralone (12.1 g, 0.04 mole, 80% yield), mp 128.5°-129.5°, [Lit. Kieboom et al., Synthesis, 476-478, (1970), mp 130°-130.5°].

Workup

  1. additionAfter the addition
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customThe pure product was obtained by recrystallization from methanol
  5. customto yield

Sources & evidence

ORD record
ord-6bdf1f91ffb341fbb6ad00a1494f428b
Source dataset
uspto-grants-1994_03
Patent number
US05296508

Reaction notes

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